#------------------------------------------------------------------------------
#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/48/4034816.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4034816
loop_
_publ_author_name
'Usmanova, Liliia'
'Dar'in, Dmitry'
'Novikov, Mikhail S.'
'Gureev, Maxim'
'Krasavin, Mikhail'
_publ_section_title
;
 Bicyclic Piperazine Mimetics of the Peptide β-Turn Assembled via the
 Castagnoli-Cushman Reaction.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5859
_journal_page_last               5868
_journal_paper_doi               10.1021/acs.joc.8b00811
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C17 H20 F N3 O3'
_chemical_formula_sum            'C17 H20 F N3 O3'
_chemical_formula_weight         333.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_date             2017-11-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                89.339(3)
_cell_angle_beta                 77.612(3)
_cell_angle_gamma                80.243(3)
_cell_formula_units_Z            2
_cell_length_a                   6.8496(3)
_cell_length_b                   10.1390(4)
_cell_length_c                   12.0844(4)
_cell_measurement_reflns_used    6902
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.7540
_cell_measurement_theta_min      3.7120
_cell_volume                     807.57(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω      6.00  64.00   1.00    2.50    --   40.38 -99.00   0.00   58
  2  ω     48.00 144.00   1.00   10.00    --  113.00 -30.00 120.00   96
  3  ω     84.00 178.00   1.00   10.00    --  113.00  15.00   0.00   94
  4  ω    125.00 168.00   1.00   10.00    --  113.00  45.00 -90.00   43
  5  ω    104.00 131.00   1.00   10.00    --  113.00 112.00-180.00   27
  6  ω     84.00 128.00   1.00    2.50    --   40.38 178.00 -60.00   44
  7  ω    123.00 175.00   1.00   10.00    --  113.00 112.00 120.00   52
  8  ω     38.00 104.00   1.00   10.00    --  113.00 -45.00-120.00   66
  9  ω     70.00  98.00   1.00   10.00    --  113.00 -95.00 -30.00   28
 10  ω     47.00 137.00   1.00   10.00    --  113.00 -77.00  60.00   90
 11  ω     43.00 139.00   1.00   10.00    --  113.00 -30.00   0.00   96
 12  ω     90.00 115.00   1.00   10.00    --  113.00-112.00-180.00   25
 13  ω     49.00  95.00   1.00   10.00    --  113.00 -95.00-150.00   46
 14  ω     39.00  64.00   1.00   10.00    --  113.00-112.00-180.00   25
 15  ω     35.00  98.00   1.00   10.00    --  113.00 -95.00 -90.00   63
 16  ω     35.00 112.00   1.00   10.00    --  113.00-112.00  60.00   77
 17  ω    -63.00 -37.00   1.00    2.50    --  -40.38 178.00 -90.00   26
 18  ω   -113.00 -17.00   1.00    2.50    --  -40.38 -57.00-120.00   96
 19  ω   -115.00 -16.00   1.00    2.50    --  -40.38 -38.00 120.00   99
 20  ω   -121.00 -43.00   1.00    2.50    --  -40.38 178.00 -30.00   78
 21  ω    -61.00  24.00   1.00    2.50    --  -40.38  38.00 -60.00   85
 22  ω   -116.00 -14.00   1.00    2.50    --  -40.38 -38.00 -60.00  102
 23  ω     12.00  38.00   1.00    2.50    --   48.00  84.00 131.35   26
 24  ω     12.00  37.00   1.00    2.50    --   48.00  84.00-138.32   25
 25  ω     18.00  43.00   1.00    2.50    --   52.00  80.00  33.04   25
 26  ω     17.00  42.00   1.00    2.50    --   52.00  81.00 -80.64   25
 27  ω     17.00  44.00   1.00    2.50    --   52.00  82.00 -26.56   27
 28  ω     33.00  59.00   1.00    2.50    --   64.00  76.00  71.97   26
 29  ω     31.00  69.00   1.00    2.50    --   64.00  76.00 110.94   38
 30  ω     97.00 140.00   1.00    2.50    --   64.00  76.00 -79.17   43
 31  ω     32.00  58.00   1.00    2.50    --   64.00  76.00 -79.17   26
 32  ω     34.00  65.00   1.00    2.50    --   68.00  77.00-121.77   31
 33  ω    107.00 144.00   1.00    2.50    --   68.00  70.00 -19.56   37
 34  ω     38.00  63.00   1.00    2.50    --   68.00  70.00 -19.56   25
 35  ω     36.00  62.00   1.00    2.50    --   68.00  75.00 169.75   26
 36  ω     35.00  64.00   1.00    2.50    --   68.00  75.00  21.03   29
 37  ω     39.00  70.00   1.00    2.50    --   72.00  76.00  38.17   31
 38  ω     44.00  77.00   1.00    2.50    --   72.00  60.00-151.81   33
 39  ω     43.00  74.00   1.00    2.50    --   76.00  72.00  81.94   31
 40  ω     57.00  93.00   1.00   10.00    --   88.00  71.00 -72.56   36
 41  ω     79.00 105.00   1.00   10.00    --  113.00  77.00 -30.00   26
 42  ω    120.00 146.00   1.00   10.00    --  113.00  77.00  60.00   26
 43  ω     79.00 112.00   1.00   10.00    --  113.00  77.00  60.00   33
 44  ω     83.00 131.00   1.00   10.00    --  113.00  61.00-120.00   48
 45  ω     87.00 114.00   1.00   10.00    --  113.00  61.00 -60.00   27
 46  ω     79.00 153.00   1.00   10.00    --  113.00  77.00 120.00   74
 47  ω     80.00 118.00   1.00   10.00    --  113.00  77.00-180.00   38
 48  ω     83.00 123.00   1.00   10.00    --  113.00  61.00 -90.00   40
 49  ω     85.00 111.00   1.00   10.00    --  113.00  61.00 -30.00   26
 50  ω     81.00 139.00   1.00   10.00    --  113.00  77.00   0.00   58
 51  ω     79.00 105.00   1.00   10.00    --  113.00  77.00 -90.00   26
 52  ω     86.00 142.00   1.00   10.00    --  113.00  61.00  90.00   56
 53  ω     87.00 129.00   1.00   10.00    --  113.00  61.00 120.00   42
 54  ω     84.00 111.00   1.00   10.00    --  113.00  61.00   0.00   27
 55  ω    125.00 151.00   1.00   10.00    --  113.00  77.00 150.00   26
 56  ω     85.00 159.00   1.00   10.00    --  113.00  45.00-180.00   74
 57  ω     79.00 105.00   1.00   10.00    --  113.00  77.00 150.00   26
 58  ω     79.00 116.00   1.00   10.00    --  113.00  77.00-150.00   37
 59  ω     79.00 105.00   1.00   10.00    --  113.00  77.00 -60.00   26
 60  ω    133.00 166.00   1.00   10.00    --  113.00  77.00  90.00   33
 61  ω     85.00 110.00   1.00   10.00    --  113.00  61.00  30.00   25
 62  ω     79.00 129.00   1.00   10.00    --  113.00  77.00  30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13308
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.482
_diffrn_reflns_theta_min         3.746
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       prism
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         3213
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0349
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0460P)²+0.2734P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0929
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2857
_reflns_number_total             3213
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b00811_si_007.cif
_cod_data_source_block           103-428-7402_ulm684
_cod_database_code               4034816
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.847
_shelx_estimated_absorpt_t_min   0.777
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
F24 F 0.78596(17) 0.28273(10) 0.43477(9) 0.0536(3) Uani 1 1 d
O14 O 0.14274(13) 0.83522(9) 0.16314(8) 0.0224(2) Uani 1 1 d
O12 O 0.69528(13) 1.00732(8) 0.09843(8) 0.0212(2) Uani 1 1 d
O13 O 0.69495(15) 0.57700(9) -0.12926(8) 0.0274(2) Uani 1 1 d
N6 N 0.66579(15) 0.68514(9) 0.03769(8) 0.0155(2) Uani 1 1 d
N9 N 0.42559(15) 0.83058(10) 0.23311(8) 0.0164(2) Uani 1 1 d
N2 N 0.88428(15) 0.89627(10) -0.05995(9) 0.0174(2) Uani 1 1 d
H2 H 0.890(2) 0.9754(18) -0.0878(14) 0.025(4) Uiso 1 1 d
C8 C 0.32806(18) 0.79920(11) 0.15482(10) 0.0170(2) Uani 1 1 d
C1 C 0.77816(17) 0.90138(11) 0.04803(10) 0.0159(2) Uani 1 1 d
C11 C 0.75895(17) 0.76613(11) 0.10391(10) 0.0145(2) Uani 1 1 d
H11 H 0.889(2) 0.7185(14) 0.1076(12) 0.013(3) Uiso 1 1 d
C5 C 0.77458(19) 0.62920(11) -0.06340(10) 0.0185(2) Uani 1 1 d
C10 C 0.64043(17) 0.77949(11) 0.22636(10) 0.0154(2) Uani 1 1 d
H10 H 0.694(2) 0.8434(14) 0.2629(12) 0.013(3) Uiso 1 1 d
C16 C 0.67264(18) 0.64690(12) 0.28645(10) 0.0181(2) Uani 1 1 d
C3 C 1.01840(18) 0.78560(12) -0.13024(10) 0.0180(2) Uani 1 1 d
H3A H 1.159(2) 0.7977(16) -0.1368(13) 0.022(4) Uiso 1 1 d
H3B H 0.986(2) 0.7954(15) -0.2066(13) 0.019(4) Uiso 1 1 d
C23 C 0.8486(2) 0.61146(13) 0.32818(11) 0.0240(3) Uani 1 1 d
H23 H 0.945(3) 0.6710(18) 0.3231(14) 0.031(4) Uiso 1 1 d
C7 C 0.44477(18) 0.71675(12) 0.05103(11) 0.0190(3) Uani 1 1 d
H7A H 0.391(3) 0.6341(17) 0.0544(14) 0.028(4) Uiso 1 1 d
H7B H 0.409(2) 0.7668(16) -0.0125(14) 0.025(4) Uiso 1 1 d
C4 C 0.99628(19) 0.64325(12) -0.09145(10) 0.0187(2) Uani 1 1 d
H4A H 1.062(2) 0.5826(16) -0.1534(14) 0.023(4) Uiso 1 1 d
H4B H 1.064(2) 0.6188(15) -0.0277(13) 0.021(4) Uiso 1 1 d
C15 C 0.31556(19) 0.90572(13) 0.33706(11) 0.0206(3) Uani 1 1 d
H15A H 0.359(3) 0.8551(17) 0.4009(14) 0.027(4) Uiso 1 1 d
H15B H 0.175(3) 0.9053(16) 0.3413(13) 0.025(4) Uiso 1 1 d
C19 C 0.5369(2) 0.55769(13) 0.29514(11) 0.0242(3) Uani 1 1 d
H19 H 0.417(3) 0.5766(18) 0.2643(15) 0.034(4) Uiso 1 1 d
C21 C 0.7482(2) 0.40390(15) 0.38638(12) 0.0338(3) Uani 1 1 d
C17 C 0.3564(2) 1.04872(13) 0.34028(11) 0.0237(3) Uani 1 1 d
H17A H 0.504(3) 1.0475(17) 0.3293(14) 0.028(4) Uiso 1 1 d
H17B H 0.307(3) 1.0975(17) 0.2774(15) 0.028(4) Uiso 1 1 d
C22 C 0.8878(2) 0.48842(15) 0.37834(11) 0.0319(3) Uani 1 1 d
H22 H 1.005(3) 0.4629(19) 0.4041(17) 0.044(5) Uiso 1 1 d
C18 C 0.2516(2) 1.11656(15) 0.45445(13) 0.0321(3) Uani 1 1 d
H18A H 0.280(3) 1.207(2) 0.4588(18) 0.055(6) Uiso 1 1 d
H18B H 0.293(3) 1.063(2) 0.5185(18) 0.046(5) Uiso 1 1 d
H18C H 0.104(3) 1.121(2) 0.4679(18) 0.051(6) Uiso 1 1 d
C20 C 0.5748(2) 0.43406(15) 0.34517(13) 0.0330(3) Uani 1 1 d
H20 H 0.481(3) 0.372(2) 0.3527(18) 0.052(6) Uiso 1 1 d
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0180 0.0090 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0730 0.0530 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0310 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0490 0.0320 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C11 N6 C7 117.31(9)
C5 N6 C11 119.60(9)
C5 N6 C7 116.92(10)
C8 N9 C10 122.24(10)
C8 N9 C15 121.08(10)
C10 N9 C15 116.31(9)
C1 N2 C3 131.61(10)
O14 C8 N9 122.86(12)
O14 C8 C7 117.44(10)
N9 C8 C7 119.70(10)
O12 C1 N2 122.49(11)
O12 C1 C11 121.33(10)
N2 C1 C11 116.14(10)
N6 C11 C1 110.15(9)
N6 C11 C10 109.91(9)
C10 C11 C1 113.29(9)
O13 C5 N6 121.82(11)
O13 C5 C4 122.65(11)
N6 C5 C4 115.44(10)
N9 C10 C11 111.31(9)
N9 C10 C16 111.86(9)
C11 C10 C16 110.79(9)
C23 C16 C10 118.87(11)
C19 C16 C10 121.72(11)
C19 C16 C23 119.32(12)
N2 C3 C4 116.72(10)
C22 C23 C16 120.41(13)
N6 C7 C8 116.66(10)
C5 C4 C3 110.13(10)
N9 C15 C17 113.31(10)
C16 C19 C20 120.74(13)
F24 C21 C22 118.74(14)
F24 C21 C20 118.11(15)
C20 C21 C22 123.13(13)
C18 C17 C15 110.33(11)
C21 C22 C23 118.33(13)
C21 C20 C19 118.06(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F24 C21 1.3634(16)
O14 C8 1.2425(15)
O12 C1 1.2276(15)
O13 C5 1.2267(15)
N6 C11 1.4607(14)
N6 C5 1.3606(16)
N6 C7 1.4672(15)
N9 C8 1.3389(16)
N9 C10 1.4600(15)
N9 C15 1.4654(16)
N2 C1 1.3474(16)
N2 C3 1.4705(15)
C8 C7 1.5095(18)
C1 C11 1.5349(15)
C11 C10 1.5228(16)
C5 C4 1.5141(17)
C10 C16 1.5260(16)
C16 C23 1.3951(17)
C16 C19 1.3910(18)
C3 C4 1.5342(15)
C23 C22 1.391(2)
C15 C17 1.5248(17)
C19 C20 1.3942(18)
C21 C22 1.376(2)
C21 C20 1.371(2)
C17 C18 1.5237(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168328676
